


Fallen Angel

by cryptomoon, firefly124, justholdstill, LegendsofSnark, MaskofCognito, NadiaHart, RavensCAT, SailorKamenRider, smudgythoughts, supernatural9917, thatpeculiarone, uncelestial



Category: Supernatural
Genre: Alternate Universe - Human, Alternate Universe - Noir, Detective Castiel, Detective Noir, M/M, POV Castiel, POV Dean, POV First Person, Profound Robin Round 2, Round Robin, profoundnet
Language: English
Status: In-Progress
Published: 2018-04-19
Updated: 2018-07-04
Packaged: 2019-04-24 22:50:48
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 12
Words: 17,375
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14365377
Author URL: https://archiveofourown.org/users/cryptomoon/pseuds/cryptomoon, https://archiveofourown.org/users/firefly124/pseuds/firefly124, https://archiveofourown.org/users/justholdstill/pseuds/justholdstill, https://archiveofourown.org/users/LegendsofSnark/pseuds/LegendsofSnark, https://archiveofourown.org/users/MaskofCognito/pseuds/MaskofCognito, https://archiveofourown.org/users/NadiaHart/pseuds/NadiaHart, https://archiveofourown.org/users/RavensCAT/pseuds/RavensCAT, https://archiveofourown.org/users/SailorKamenRider/pseuds/SailorKamenRider, https://archiveofourown.org/users/smudgythoughts/pseuds/smudgythoughts, https://archiveofourown.org/users/supernatural9917/pseuds/supernatural9917, https://archiveofourown.org/users/thatpeculiarone/pseuds/thatpeculiarone, https://archiveofourown.org/users/uncelestial/pseuds/uncelestial
Summary: Castiel Novak is a former beat cop turned private detective. He spends his days doing the work the cops won’t, and spends his nights at Harvelle’s Speakeasy. His life isn’t quiet, but it’s predictable. That is until a man with big green eyes, long legs, and a story about a missing kid brother shows up at his agency.





	1. Chapter 1

**Author's Note:**

> Welcome to Round 2 of the Profound Robin! The Profound Robin is a round robin challenge hosted by the ProfoundBond discord. 
> 
> If you haven’t heard of it before, a round robin is a story where each chapter is written by a different author. We had a ton of fun with the last round and hope you’ll enjoy this as much as we’re enjoying writing it.

**Summary for the Chapter:**

> The first chapter is written by me, Cryptomoon, I hope you enjoy!

It had been one _hell_ of a day.

This morning I woke up feeling like I had been kicked hard in the skull, a bit too much gas the night before, but I was able to shake it off with a little help from my old friend John Jameson.

On the way uptown I got snagged by Officer Singer and dragged into the cop shop to answer a bunch of questions about some missing boy I’d never heard of. Bobby’s a good man, better than most of the cops in this town, and something about this missing kid’s got him grasping at straws. He wanted to know if anyone had solicited my services over the past few days. If I’m worth my salt I’d say the guy’s got a personal connection to the case. After an hour of sitting on my ass and then another fielding questions I didn’t have the answers to, he cut me loose.

I was already late as hell to the gig I had lined up, and the bucket of bolts I call a car took her sweet time getting warmed back up. It was well past noon by the time I made my way to the job.

I was supposed to be keepin’ an eye on little Miss Harvelle for her battle axe of a mother. I wanted to wrap it up as quick as possible. Ellen Harvelle was a good woman and a better purveyor of hooch. She ran The Roadhouse, the seediest speakeasy in town. That dame managed to survive the prohibition with her ass outside a jail cell and her books in the black on her moxie alone. And, well, Ellen _never_ missed a word uttered at her bar. I owe her big time for tips she’d slipped me alongside two fingers of Old Crow. Checking up on Joanna Beth was the least I could do.

The surveillance I had planned was shot when I pulled my hunk of rust up to Benny’s just in time for Jo and her friend Meg to tumble out the door, cackling like a couple a magpies.

Jo shoved the other girl aside and bounced over to the passenger window as soon as she saw me. “Heya, Mr. Novak! You headin’ over to my mom’s joint?”

I squinted at her. Joanna Beth was seventeen, but with her messy blonde ponytail and boy cut trousers she looked like the same little girl who’d taken me for my very last dollar at poker over ten years ago. Ellen thought Jo was hanging around with older boys, but I’d only ever seen her with the short brunette currently smirking and rolling a cigarette on the hood of my car. “No, Joanna. I’ll be in later this evening, but I’m running late to the office as it is.”

Jo swiped the newly rolled cigarette out of her friends mouth and leaned into the car window, “Got a light?”

I rolled my eyes high as as I flicked open my lighter and held the flame to the end of the smoke, “Don’t let your mom catch you smoking or she’ll tan your hide.”

Jo took a long drag and grinned wide. “You don’t tell her I’m smokin’ and I won’t tell her you're the one that lit it for me.”

I raised my eyebrow and frowned at the girl, snapping the lighter shut with a sharp click. “It’s a deal.”

“Come on, Jo.” Meg tugged on Jo’s sleeve and threw a wink over her shoulder at me. “Later, Mr. Spade.”

The girls were around the corner of the parking lot and outta my sight before I could blink. I was thoroughly confused. My name is _not_ Spade.

I shook off the interaction and made my way into Benny’s Diner. Now, Benny’s wasn’t the classiest dive in town, but the man could make a damn fine cup of coffee.

I dropped into my usual seat at the counter and took a deep breath. The place always smelled like fresh coffee, charred burgers, and cherry pie. It’s like the weight of the whole world fell off my shoulders right then. I could die in a place like this and I’d die a content man.

A low chuckle from the direction of the kitchen drew my eyes to the rough looking proprietor leaning in the doorway. “Evenin’, Officer Novak. I saw your bucket a’ bolts drag itself into my lot and started you a pot a’ joe. You’ve looked a sight better, brother.” Benny wiped his greasy hands on an even greasier rag. “Rough day?”

“I am not an officer any more, Benny. You know that.” I sighed and set my hat on the counter next to me. “I’ve had a rough day and a rough night before that.” I pinched the bridge of my nose hard. That damned headache from this morning was coming back.

Benny didn’t bother responding to the correction. Just like every day before today and probably every one after tomorrow. “I’ll grab ya that cup.” The man winked at me and turned away to pour the coffee I so desperately needed.

“Today has been a strange day, Benny.” I paused as he slid the cup in front of me, black as midnight on a moonless night. It was hot as hell, but tasted just like heaven. “Thank you. Today has been a _strange_ day. It’s like I stepped out of bed and the world was one step ahead. I haven’t been able to catch up since.”

Benny shook his head, “I’ve had those days, bo, you just gotta push through until you get back to your bed and start over tomorrow.” The man shrugged his broad shoulders before smiling wide. “Maybe this’ll turn that streak around. Andrea wanted to thank you for trackin’ down that punk that knocked us over last week.” He reached into the display of pies on the edge of the counter and pulled out a fat apple pie before sliding it into a box and pushing it across the counter toward me.

“That’s really not necessary, Benny.” And it wasn’t necessary, but I certainly hoped he wouldn’t agree. The pie smelled as good as the coffee and I quickly realized I hadn’t eaten anything since the night before.

“Break it up, Novak, It’s yours.” Benny turned me away with a stern frown when I reached into my coat for my billfold.

I sighed and slipped my hat back on. “You give that wife of yours a squeeze from me and then a kiss for the pie.” I quirked a smile at him and drained the last of my coffee. It was into the afternoon and I still hadn’t made it into the office.

Benny grinned and waved me off before retreating to the kitchen.

I pushed my way out of the diner and back to my car.

When I pulled up outside the ugly building that housed my office, there was a big black car parked out front. Now, I didn’t know a whole lot about cars. I knew enough to keep mine mostly running and enough to tell that this one was either owned by someone who loved her or someone who could pay someone to make it seem like they did. It wasn’t often you saw a girl like her in this part of town and I was intrigued.

I didn’t bring in a ton of dough as a dick. I got a soft spot for this town bigger than that Chevy sitting in my parking spot outside. I had a bad habit of doing what’s right, and as my recent career change might imply, that didn’t always pay off. As such, my office was just a basement apartment next to the boiler room in a building older than the Bible.

As I shoved the door closed behind me, Mrs. Mosley poked her head out of her front door and narrowed her eyes at me, shaking her head.

“Castiel, sweetheart, you need to take better care of yourself.” She clicked her tongue and put her fists on her wide hips. “You cannot keep runnin’ round half the night chasin’ after the riff raff and then spendin’ the other half up at Harvelle’s! You’re runnin’ yourself ragged, child.”

“How do you know what I—“ I didn’t need to ask, really, I knew she wasn’t going to answer with anything other than a smack to the back of my head.

She cuffed me lightly, knocking my hat forward across my eyes, “Don’t ask stupid questions, Castiel Novak.” She huffed and rolled her eyes. “Now, there is a boy down in your office, and he’s been waiting for some time. I let the poor thing in for you. He looks about as worried as a turkey in November. You go do what you do best and help him find what he lost.” She pushed my hat back into place and patted my cheek before turning on her heel and retreating into her apartment.

Missouri had an uncanny ability to read people, and if she said this man lost something, I’d bet my reputation that he did.

So there I was standing like an idiot in the lobby of the musty brick building I call my place of employment and nursing an ever expanding headache.

It had to be a side effect of the weird day I had, but it felt like i was standing on the edge of something. That feeling you got when you’re up on that big rock at the quarry and you knew you’re about to jump in the water. Excited and nervous in a way that made everything inside you feel ready to scream.

I had half a mind to turn around, get back in my car, and just drive back home. It felt like the safe thing to do, but I’d never been good at the safe thing. So, I jogged down the stairs and pushed open the door to my office only to stop short at the sight of my potential client.

When Missouri said _boy_ I was expecting some lanky teenager, not someone like the man sitting on the corner of my desk. No, this man was anything but a boy.

**Notes for the Chapter:**

> As someone who has never written first person before, this was a challenge! It was fun as heck though.
> 
> I really hope you guys enjoyed this first chapter! Next author up is RavensCAT!


	2. Chapter 2

**Notes for the Chapter:**

> Hey y'all, so I (Ravenscat) got put up right after Crypto's amazing chapter, which, thanks for the pressure everyone. Anyways, I did my best and I hope y'all enjoy!

It had been one _hell_ of a day.

No, scratch that. It had been one _hell_ of a week.

Sam had been driving me crazy for a week and then he just disappeared, which wasn’t like him at all. He would have at least checked in.

I mean he’s my kid brother, well… technically because that boy is growing like Jack’s beanstalk, but I should’ve taken better care of him.

At this point, I didn’t know what to do, so I called Bobby. He said he would do everything he could and also advised me to go meet someone name Castiel, what kind of name is that? Apparently, he was some private detective and he was really good at his job. I mean, it’s worth a shot. Anything to find Sammy.

Since I had work I couldn’t go down to meet Castiel right away. I couldn’t afford to take the day off or we would go flat. I needed the dough, to care for Sammy and me.

I don’t know how I managed to get through work because every 20 minutes or so, I was checking the time

I needed to find my baby brother now, I couldn’t wait any longer so I took the last hour off and rushed to Castiel’s office. Bobby had given me the address earlier in the day.

Once I got there I looked at the old ugly building. I mean I’m not one to judge, I know how it is to be on the nut, as long as this guy does his job as well as people say he does.

I yanked on the door and it make a loud obnoxious squeaking noise as it opened. I winced and walked in.

I headed down the stairs towards the basement where Castiel’s office was.

I looked at the number on the paper I had written the address on to make sure it was the right room before I knocked.

No one opened the door.

I tried again and still no answer.

I sighed, great, this was wonderful. The guy wasn’t here.

I leaned against the opposite wall and slid down it. I pulled my knees up and waited.

After a couple minutes, I heard the basement door open and a dame peeked her head out.

“You here for Castiel, sweetheart?” She asked me.

I nodded, “Yes, mam. Is he going to be here soon?” I asked, standing up.

“He should be. I’m Missouri Mosely” She said stepping down the last stair and holding her hand out for me to shake.

I grabbed her hand and she gave it a good tight squeeze.

“Come, I’ll let you in boy. You look like you could use a chair and some sleep.”

I laughed, rubbing at my eyes.

“You’re not wrong.” I said.

She unlocked the door to Castiel’s office, which was just a single shabby looking apartment.

“There you are, honey.” She said as she let me in.

“Thank you, Mrs. Mosely.” I said as I stepped into the room.

“You’re welcome. I hope you find what you’ve lost.” She said before she walked away.

I frowned, watching her go. How did she know? The woman seemed nice, but she gave me the shivers. The way she looked at me like she could see my life and my future was kind of creepy.

I shook it off and inspected Castiel’s office. It was simple and even with the light it was dark. There was a table towards the back of the room with a chair on either side. There was a filing cabinet against the back wall beside the office chair, where I suspected Castiel sat.

The walls were naked except for the dried water stains from a leak, who knows how many years ago. The room had a slight mildew smell but I guess it’s a given, considering how old this building is.

I went over and rested my keister comfortably on the corner of Castiel’s desk, legs spread, while I waited for him.

I grabbed a phot of Sam out of my pocket, fiddling with it, just so I had something to do with my hands while I waited.

Twenty minutes later I heard the doorknob turn. I raised my head to look at Castiel.

When I heard the name _Castiel_ , I had expected an ugly old bald guy, with a handlebar mustache and a beer belly. Not someone like who just walked in. No, this guy was _anything_ but old or ugly.

**Notes for the Chapter:**

> Ahh, so I hope everyone enjoyed that. Next author up is Jess, thatpeculiarone (ilovetodream).


	3. Chapter 3

**Notes for the Chapter:**

> Hey guys I'm Jess (thatpeculiarone). I'd like to thank everyone on their support of this fic so far! This was such a challenging thing for me to write as I rarely write in first person and I have never written in the Noir style before! It was very different, but I hope you enjoy!!

When I first set my eyes on the man in my office, all I could think about was the appeal he had on the eyes.

 

Now, it wasn’t a common thing for me to do, have thoughts about how much of a looker another fellow is. Yet, I couldn’t help it upon seeing the man in front of me, sitting on my desk with an odd aura of insecurity to him. There were features about him that made him look quite young: such as his small frame and the childlike innocence that he seemed to manifest. Though I also couldn’t ignore his rugged appearance, or his devilishly long legs which seemed to go on for miles compared to my own. I couldn’t also help but notice the hardness around the edges of his pale green eyes. In my line of career, misfits are the main source of my work. Those poor hoods and criminals that have been the mark of the world dozens of times. The man waiting for me had this look, a look that described the life that he lived until that point, and it was something that couldn’t be seen in no boy.

 

The man’s stare met mine as soon as I walked into the room and after a moment of hesitation, he was quick to stand, holding his hand out.

 

“Dean Winchester, sir.” The man, _Dean_ , spoke. His voice was deep. _Definitely_ a man’s voice.

 

“Castiel Novak. Please, don’t call me sir.” I replied, shaking his hand, noting how firm but tender his grip was. He let go and I walked past him to take a seat. Dean stood awkwardly, until I indicated to the chair next to him, which he calmly slipped into.

 

“So, what can I do for you today, Mr. Winchester?” I asked, leaning back in my chair. Dean shifted uncomfortably, before looking me in the eye with a steady gaze.

 

“Just call me Dean, Mr. Winchester is my father’s name.” Dean replied, a wry smile on his lips. “And Bobby sent me, said you were the best detective he’d seen in years. Said that if anyone could help me, it would be you.”

 

“Officer Singer?” I asked in surprise, to which Dean affirmed.  Officer Singer was a surly old geezer, who had a lack of manners worse than some of the crooks we had locked up in the big house. He wasn’t the one to say nice things, in fact, I don’t think I’d ever heard a kind word come out of his mouth. I was pleasantly chuffed to hear about his glowing recommendation to Dean.

 

“My brother is missing.” Dean continued, passing me a small photograph. It was of a boy and this time, it was _definitely_ a boy. He looked no older than sixteen years of age, with cherub cheeks and floppy hair. He had a serious expression on his face, however, I could see the brightness in his dark eyes and the way they crinkled at the side. I could tell that despite how solemn he looked in the photograph, this boy was anything _but_ solemn.

 

“He’s only a kid,” Dean continued, “He’s barely old enough to be in the workforce, let alone to leave home. We’re all each other has, so I know he wouldn’t leave town without letting me know where he was heading. He’s too good to do that.”

 

I took one last stare at the photograph before putting it down, turning my attention back to Dean.

 

“Why aren’t the cops looking into this? Why can’t they or Officer Singer help you?”

 

Dean rolled his eyes. “The coppers don’t know from nothing. They think because I grew up in the slums that I’m out to be some sort of grifter or something. They think Sammy just decided to breeze off, without even letting me know. Said that’s the way our kind roll.”

 

I wasn’t surprised in the least about Dean’s bitterness towards my once fellow officers. For being cops, they were highly opinionated and quite corrupt. One of the many reasons I was no longer one myself.

 

“So Sammy… is that your brother?” I asked, causing Dean to crack a grin.

 

“Yeah, but he goes by Sam. Don’t let him hear you call him Sammy, otherwise he’d probably cut you down.”

 

It took a moment for me to understand that Dean was telling a joke, so I forced a smile in response.

 

“So Sam… he’s the one who’s missing.” I clarified, remembering the unpleasant encounter I had that morning. I had been right about the fact that Officer Singer had a personal connection to the missing kid. It would only be a Death’s door that he would ever solicit my services to someone; Sam must have been someone close to him, in order for him to recommend myself to Dean.

 

“Yeah, Bobby can’t get the cops to help out much, which is why he told me to come to you. Said if anyone would be able to get my brother home, it would be you. Swore on his mama’s grave.”

 

“I promise I will do my best.” I said earnestly, reaching into my desk drawer to pull out my notepad and pen.

 

“So… you’ll help me?” Dean uttered, his eyes wide and hopeful.

 

“Of course,” I replied, “Now tell me what happened?”

 

“Well I got home last week, at my usual time, and couldn’t see Sammy anywhere, so I…”

 

“Stop.” I interrupted causing Dean to look at me confused. “To help find your brother, I need to know every little detail. I need to know what happened over the past few weeks. Did anything suspicious happen? Anything out of the ordinary? Anything shady? I need to know every little dime of information that you have.”

 

I folded my hands together, sat up straight and looked Dean straight in the eye.

 

“So Dean… tell me _everything_.”

**Notes for the Chapter:**

> Thanks again for reading! Next author up is the one and only (and absolutely lovely) NadiaHart!


	4. Chapter 4

**Summary for the Chapter:**

> The Games Afoot

**Notes for the Chapter:**

> Hello Hello! Thank you for stopping by for my chapter. I'm very excited to be taking part in the RoundRobin again. I've never written in first person perspective and it was both challenging and addicting! I would like to recommend some ambient music to go along with this fic. It really, really sets the mood.
> 
> [-The Back Alley-](https://youtu.be/0mwOYj4uqf0?t=31s)
> 
> As always special thanks to the [ProfoundBond Discord](https://discord.gg/GGbw2NP) for running this and for all the constant encouragement.
> 
> The ever wonderful [HarplessCastiel](http://harplesscastiel.tumblr.com/) is my beta and don't blame them for the 'says', they told me not to use it but I did anyway.
> 
> Anyway click the music and dig in, things are about to get... _dramatic_ but that's why you're here, after all, this is Noire. 
> 
> (there's a glossary of Noire terms in the endnotes)

I could smell a lie like a slice of hot apple pie coming down the counter at Benny’s. It’s a learned thing, some say, but for me, it’s always been natural. You gotta observe, gotta pay attention to the little details. Things you see on the blurry edges of your vision, the things other folks pay no mind to, but you gotta see ‘em, gotta notice ‘em, when you deal with the demons and heathens lurkin’ in the shadowed belly of a town like mine. When you live a life on the edge of the light and the dark like I do.

It’s all in the way the corners of the lips dip, or how the shoulders raise just a margin, how the eyes slide away and back, away and back again, and Dean, lovely as he is–as he licks his lips and rubs his palms together–is giving me all the signs of a lie.

“So,” I says, circling around my desk to bring myself closer to the man, to really get the look of his eye without miles of rough broken desk between us. “If I’m going to help you, and I am, I need the truth. Not just what you want me to hear. What you _think_ will get me in your pocket.”

  
Dean pauses just long enough to watch my gait as I stroll around and sidle up onto the edge of my desk. The way his crisp green gaze slings low along my hips for a mite longer than would be considerate makes me lick my lips. There’s somethin’ there, somethin’ the kid ain’t telling me, and maybe if he’d wandered through my door on a different day, maybe if he weren’t clutchin’ that photo, and singing the song of a missing brother, we’d be havin’ a different, conversation right about now. A conversation that involved less words, less clothes... but he ain’t, so we ain’t.

Slipping my hat from my head, I rest it on the curl of my knee. Dean slumps like he’s got the weight of the world on his shoulders. “Nothin’ and nobody’s going to be able to help you if you’re spinning false here, boy.” I says, and a muscle in Dean’s jaw jumps angrily.

“I ain't-a boy.” He snaps, eyes narrowed, lips pursed.

“Then don’t act like one; I don’t have all day to sit here and try to pry the…”

“The canary down at Lucian’s.” Dean starts, cutting in on my tirade. “Lovely bird, if you’re... _into_ that sorta thing.” His eyes flash liquid heat, from behind long dark lashes, and I can’t help but reach for a distraction, anything to break the implication behind Dean’s words, his gaze.

I reach for my smokes, pulling out a deck. I slip a gasper between my teeth before offering one to the temptress sitting in the chair before me. He takes one and I light them both for us. Smoke curls between us like the slow swaying hips of the chippy’s dancin’ at the drum each Saturday night. Dean’s lips wrap around the end of his smoke and he pulls the vapors in, speaking around his exhale like it isn’t something sinful. “Got a voice like nothin’ you ever heard before.”

  
“I know the dame,” I says, drawing in my own hit of nicotine to keep my thoughts on the straight and narrow. “Ruby Calhoon.”

  
“That’s the one,” Dean says, leaning forward to ash in the small glass dish next to my thigh. “Anyway, Sammy’s got it in his head that the dame’s in it for him, that her eyes shine only for him. Diamonds, you know?” Dean sighs, pulling on the smoke again, “She’s got him curled ‘round her finger like it ain’t anything.”

  
I find my thoughts wandering, to dark nights, a steamy atmosphere’s, hidden away in the belly of an abandoned warehouse nestled just past the shipyard, under a cloak of salty ocean air where The Caged Bird sits. Lucian’s place, the only speakeasy the coppers ain’t never dared to break up. You’re more likely to see the commissioner settled in a private booth, tucked away suckin’ down hooch, than anything. Lucian is a powerful man, a man no sane sloothe would tangle his web into. My eyes cast towards Dean as he purses his lips and breathes out smoke, letting the thick fog curl back up and into his nose again like he’s not even aware he’s doing it. Like he doesn’t know what it does to me.

Lucian has his claws deep into this city, drugs, and booze, and gamblin’. Takin poor swindlers and making suckers out ‘em. He ain't never dug so deep to go after high school kids though. Lucian has his sights set on big game. City council, the mayor, everyone tucked neatly into one of his pockets. An eightball. I can’t wrap my head around why this Sam Winchester would garner appeal to the mobster, enough so that Lucian would turn his favorite lady on the boy.

I can see it, though, real easy. The sway of Ruby in her bright yellow gown, up on the stage, purring. Her voice husky and wine red into the microphone as the dancers sway to her siren call. She always weaves a spell over the crowd, it’s easy, with her dark hair, dark eyes, and darker voice. Waves of black fall like a curtain of velvet from her head to her hips, stark against the cream of her skin, honey brown eyes that can absorb a man's soul easy as winking. It’s no a surprise how a kid like Sam could get swept up with broad like that.

“Sammy ain’t got two stones to rub together when it comes to dames,” Dean says like he knows a thing or two about being burnt. “I should’a seen it sooner, the way he’d been going dark on me. Even the pretty bird who lives ‘cross the way tried to tell me. Says’ he’d been missin’ classes, sleeping through lessons. Good girl, Jessica, a pretty thing with hair like gold…” Dean pauses again, licking his lips, eyes flicking up to my own, swirling with something I can’t even begin to hope is real from a man like Dean. “If you’re into that sorta thing... that is,” he says again, slyly, like I didn’t hear him the first time. Like I could ignore it again if I wanted to, which I don’t. He reaches out, closing the scant, smoke tinted space between us and stubs his gasper in the ashtray. His fingers skim the meat of my thigh as he pulls back, languid, dangerous.

 _No_ , Dean is definitely not a boy. He plays the game like any viper who’s slithered their way into my office and pleaded their case, but Dean does it better because—as he’s been implying—Dean seeks out the same shadowed corners and hushed alleys I frequent myself. I can’t help but shift against the rough edge of my desk as my body heats to the offer Dean’s making.

“Sammy’s a good kid, always has been, too trusting, too good for this town.” Dean goes on, rubbing his palms against the stretch of his thighs. “I think he’s fallen in, I’m… worried he’s fallen in with Lucian’s Trouble Boys. I thought there was still time to get him out, to wash the stains from his hands but…”

“Now he’s missing.” I fill in, watching as Dean drops his gaze, shoulders hunched. Guilt, sadness, failure etched into each line of his lovely body. I pull my eyes away, drawing deep on my cigarette, letting the smoke fill my lungs until it burns my soul and then release it, making my decision all at once.

“This is going to be bigger than a simple lost guppy,” I says, nodding as a plan forms in my mind, where to go, who to speak with, who’s pockets to grease with the right c notes. “But we ain’t lost all hope, I’ll find him. I’ll find your Sam.” The way Dean smiles, how his shoulders lift, chest puffing out tantalizingly broad, makes me realize that I’m done for. Never has a bunny affected me so. Never has someone flashed their eyes and batted their lashes and gotten so far under my skin. I need to be careful, need to keep the lines clean…

Suddenly my arms are full of bulk, hands are gripping my back, broad and strong, a rough scratch of stubble along my neck as Dean squeezes me tight against him. Unconsciously I lean into the embrace. My only thought is … _more_.

“Thank you, Cas. You won’t regret this. I’ll make a solid partner. I’ll help…”

 _What?_ If Dean thinks he’s going to tag along like a shadow lapping at my coattails, he’s got another thing coming.

“No,” I says, pushing the man out of my space, shoving Dean back down into his chair. “I don't have partners, Dean. I work alone.” _As I should._ “You’re not trained for this life, you’re no Dick.” Dean’s smile seems to curve dark for a moment as I speak, and I can feel a flush rush up my neck. I stub my cigarette roughly, needing to escape his keen gaze and Dean bristles, standing up again, shoes scraping roughly against the floor, biting on his anger.

“I don’t know what you see when you look at me, Novak, but I ain’t some wilting daisy. I ain’t the normal waifs that stroll up in here and play their hands for your help. I’m a scrapper. I’ve been in my fair share of brawls. I’m handy with a blade and I know my way around a Tommy Gun. You ain’t sitting me out for this one, not when it’s Sammy’s life on the line.” Dean’s chest heaves with indignation, his cheeks flushed and rosy with his righteousness. He’s lovely, and I can feel myself giving into the pull of his desire. “Look at me, Cas,” he says, and even though I can tell it’s a last ditch, I can’t help but comply.

So I do, I look, with hunger, at his strong jaw, dusted with stubble, the slight thin scar running just above his left eyebrow, the impish pointed angle of his ears, and the thin, long healed slice running round the right side of his neck, like he’d just missed the killing cut of Death’s scythe. His knuckles are clenched, hands balled into fists at his sides, and they’re crisscrossed with lines that mark his wars; battles waged, battles won. There's a firmness in his stance, legs just shy of straight, attractively bowed, and ready, even now, to drop into a defensive pose. Dean’s a fighter and he’s not one to lose when the pressure’s high.

“Alright” I find myself saying, as I slide from the edge of my desk and slip my hat back onto my head.

“A––Alright?” Dean asks, melting like ice cream in the summer sun.

“Alright Dean, you can come, but you follow my lead. I don’t want you going off on your own and getting dead, ‘cause that’s the last thing I need.” I slip my coat back on and slide my deck of smokes back into the inside pocket. Opening my desk drawer I retrieve an extra box of bullets for the pistol strapped to my ribs. “Our first stop is Crowley’s. If anyone's going to have more information about Sam, about why Lucian’s set his sights on a high school kid, it’s him. His network of informants has no rival. But listen carefully, Dean. Crowley is a dangerous man, and you’re someone he’d very much like to add to his collection,” I say, licking my lips and letting my eyes slid over Dean’s form, so appealing, thinking how I’d rather keep such a treat to myself than bring him to Crowley’s attention. “Trust me to do the talkin, and we will have what we need before Ruby’s even finished her first song at The Caged Bird.”

**Notes for the Chapter:**

> Glossary:  
>  **Gaspers** : cigeretts  
>  **Deck** : Pack of smokes  
>  **Canary** : Lounge Singer  
>  **Chippy** Women Dancers at a dance hall  
>  **Drum** a Dance Hall  
>  **Trouble Boys** : Mobsters/gangsters  
>  **Dame, Bird** : a woman  
>  **Coppers** : Police  
>  **Speak Easy** : secret bar/club with a hidden entrance.  
>  **Hooch** : Booze, alcohol.  
>  **Sloothe, Dick** : Private Investigator, Private Eye  
>  **C Notes** : cash, money, hundred dollar bills  
>  **Tommy Gun** : machine gun.
> 
> Up next is [PersepHoney](https://archiveofourown.org/users/SailorKamenRider/pseuds/SailorKamenRider), so don't go far!
> 
>  _Gently pokes the Comment box, whispering:_ "Share the love."
> 
> Thanks for reading <3


	5. Chapter 5

**Notes for the Chapter:**

> This chapter won't be possible without the amazing HarplessCastiel who looked over my draft and pointed out a lot of things, also for the added Noir terms. Love ya.

I lead Dean out of my office, just in time to catch Mrs. Moseley’s eye. I tip my hat in greeting and she nods back. There’s a look in her eyes that reflects worry. Bless that woman, I swear to God she could read people like a newspaper.

 

“We taking your car or mine?” Dean asks.

 

I hold up my keys and rattle them. I won’t dare risk Crowley getting whatever information he could outta Dean, won’t let him get his hands on Dean. 

I peek into my car, assessing if it’s too cluttered, and in the same second decide it won’t matter. This is business, not some tryst. Dean slides into the passenger seat, his long legs barely stretched out in the cramped space in the car. I try to ignore the proximity of our limbs as I start the engine.

At times, our knees would touch, accident or not, and it brought back that burning feeling, heightened even more by his occasional half-lidded glances to my direction.

 

“Dean,” I speak up, trying to cut whatever air’s hanging inside the car. “There’s something you ain’t told me...…” My tongue grows heavy after that. Dean’s eyes are too damn distracting.

“Yes?” 

“How did Sam meet the skirt? Ruby? If he’s such a straight lad as you say he is. How did he end up in the Cage?”

 

I may be looking at the road, but I could feel something shift in Dean. Once again I feel his knee brush against mine and I involuntarily spare him a glance and see him worrying his lower lip.

I swallow the lump forming in my throat. “Dean. What is your brother doing in The Caged Bird?”

 

“I don’t know.” I look at him again.

“I…” Dean looks at his feet. “I’m not around much. Working late, y’know. Have to make ends meet for the two of us.”

 

The explanation struck me as unsatisfactory, but I nod nevertheless. If there’s something else underneath that statement, it’ll be evident soon enough. When we finally reach the brick building, Dean’s eye is drawn to the obnoxious sign painted on the big shop window.

 

“You’re telling me this Crowley is a newspaper man?”

 

Bells jingle as I push the door open and motion for Dean to follow me. The place is busy and we are hardly notice as I lead Dean through the mess of people, paper, and machine. There’s a door at the far end of the shop, guarded by a large man and an equally large dog.

 

“Good evening, Bart. We came to see Crowley.”

“Do you have an appointment with the boss?” the man barks.

“No, but I’m sure Juliet here don’t mind.”

 

I reach out my hand towards the black Borzoi, and she gives it a sniff before licking my hand. I smirk at Bart. He could be guarding this door, but we all know Juliet has the final say. Bart let out a dismayed sound but moves aside. After giving three knocks, we heard a drawl from the other side.

 

“This better be important, Bart.” I hear as we enter Crowley’s office.

“Well, well, what do you have for me there, Officer Novak.” I see his eyes dart towards Dean and I immediately take a side step to block him from view. 

“How many times have I told you, Crowley? I’m no longer a copper. Today I’ve come for information. I need to know if any of your newsies got a wire about what Lucian is up to these days.” Crowley’s eyebrow arch up.

 “Lucian, eh? You know we’re not actually friends.”

 “Yes, quite the opposite. That’s why I’m sure you have your rats scurrying around him.”

 

He chuckles. “Quite the smart copper.” He says in that annoying accent.

“I’ll tell you what I know.” He stands up and walks over to me. I prepare to meet him but instead he stops in front of to Dean.

“I’d rather have this one tell me.” He gives Dean an appraising look, eyes covetous.

 

I clench my hand; it’s unwise to hit Crowley in his territory and to make enemies of him, and I wouldn’t normally care. But Dean is with me and I can’t let him get dragged into an even bigger mess.

 

“No. You’re going to talk to me.”

“You don’t get to bargain with me this time, boy. Now, do we sit down and talk about this, mister?”

“Winchester.”

“Dean!” I exclaim before I am able to stop myself. Crowley turns to me, a devilish grin plastered on his lips.

 "So, Mr. Dean Winchester, may I know what brought you to employ this detective’s service?”

 

I see Dean tense up when he mentions Ruby and her connection with Sam. I hear a tinge of frustration in his voice. Dean narrates the same thing he told me, almost word for word…

 

“Tragic.” Crowley breathes, after Dean finishes his story.

 “Unfortunately, all I know is that Lucian is eyeing some business expansion. I can’t be sure if he has your boy or not. But if it’s that skank Ruby, I may have something for you.”

 

He walks back to his desk, rips off a piece of paper from a notebook, and scrawls something on it. He hands it over to Dean, and I look over the man’s shoulder to see that it’s an address.

 

“A motel?”

 “Lucian takes care of his canaries, especially that one. I hear she’s currently staying there. So if you think your brother’s with her, you might want to pay a visit.”

 

I gently nudge Dean and direct him towards the door. As we are just outside, Crowley calls to me.

 

“Officer Novak, a word.” I nod to Dean and he goes ahead.

 “Are you sure you want to butt heads with Lucian?”

 

I consider his words. “I do what my client wants me to.”

 “Hmmm. How loyal. But be careful, he ain’t named after the devil for nothing.”

 

I ignore him and instead walk out of the door. Dean is waiting for me outside, and I can see the subtle change in his mood.

 

“What did he say?”

 I shrug. “Let’s head back to the office and we’ll talk about what to do about that.” I gesture at the paper in his hand.

 

Against better judgment, I direct my car not to the office, but to Benny’s. I would’ve taken Dean to the Roadhouse but I imagine Benny’s pie would make a better meal than hooch. Besides, I could always take Dean to the Roadhouse at another time.

 

“Cas?” I hear Dean call my name, sounding worried.

 “Huh?”

 “You stopped the car. Is somethin’ wrong?”

 

I let out a curse in my head. It’s not my intention to stop, especially in the middle of the goddamn road.. My head just couldn’t wrap around  the idea of me thinking about bringing Dean to the Roadhouse and what? Talking? Drinking?

 

“I—It’s nothing. Sorry.”

 

Throughout the rest of the ride, i could feel the heat of Dean’s gaze all over me. I get that’ he’s worried, but he shouldn’t worry this much. Thankfully, we soon arrive at Benny’s and Andrea greets us as we enter the shop and leads us to a secluded booth. She hands over our menus, but I hand them right back before Dean can take a look.

 

“Two coffees, and we’ll each have a slice of your amazing apple pie, Andrea.” I smile.

 “Pie?” Dean asks.

 “Don’t you like it, honey?” Andrea asks.

 “I like it. Very much.” Dean’s eyes sparkle, and he has a goofy grin on his face.

 “Well then, coming right up, sugar.”

 

Not long after that, Benny comes out, pushing a trolley containing the coffees and a whole pie. He places them on our table and grins.

 

“Benny, we ordered just a slice.”

 “And ya have a slice. Technically, it’s a slice of big dough. No complaints, just dig in.”

 I shake my head. “Benny, you’re gonna lose money this way!” I yell after him as he returns to the kitchen.

 “Nonsense. We’ve already have enough for the day, and a bit more. Ya need to eat, brother.” He yells back.

 “You seem to be good friends.” Dean says.

 “They’re just super generous to a broke ass former cop.”

 

We start digging into the pie as we talk about our next move, Dean is adamant to accompany me until he finds his brother. And I know better than to disagree. But I make him promise to be careful.

 

“Mr. Winchester?” Our conversation stops. I turn to see a golden-haired broad standing at my shoulder.

 “Jess?” Dean asks.

 She nods. “I went to your place to drop off today’s notes for Sam but you weren’t there.”

 “Sorry, I was out on an errand. By the way, this is Castiel Novak, he’s helping me find Sam.”

 

The girl grabs my hand and shakes it vigorously.

“Oh, thank you, Mr. Novak, sir. Everyone’s pretty worried about Sam. Especially me.”

  


It’s late at night when we make it back to my office. I give Dean the box containing half of the leftover pie. We had a little argument as to who gets to keep the pie, thankfully, Andrea intervened with a brilliant solution: to split the baby.

 

“Get a good night’s rest. We have a long day tomorrow.”

 “I should be saying the same to you.” God, the grin is back.

 

He walks to his car, and without thinking, I reach out to open the door, the same time he does. The slight touch between our fingers sends a current of electricity through me and I pull my hand back.

 

“Um, good night.” I say. I meant for it to be “good bye”. Because sleuths and clients are supposed to be professional, and professional calls for good bye and not good night.

 “Good night.”

 

As I walk back to my boiler-room office, I notice that the door is unlocked. Instinctively, I grab my gun from my trenchcoat pocket. I open the switch, and instead of the attack I had been expecting, I see a fella with shaggy hair sitting in a chair. He immediately gets up to face me, a hand already outstretched.

 

“Sam Winchester?” I know the face from the pictures Dean had shown me.

 “Yes. Mr. Novak? Nice to meet you.” Even though I’m confused, I take his offer to shake hands.

 “What are you doing here, boy? Your brother’s looking for you.”

 “That’s just it. Dean’s making a mess out of things. I didn’t go missing. I left.” He says it like it’s the simplest thing in the world.

 “You’re telling me that you left on your own?”

 “Yes!” his smile is unsettling.

 “I’m sorry Sam, but I would like to talk to the one who came with you.”

 

I turn around to confirm the presence I’ve been feeling. True enough, a tall, thin man stand lurking behind the door. He smirks as he approach me and waves Sam away.

 

“Close the door, boy. This is going to be a grown up talk.”

 “Who are you?”

 “Alastair.” I hope my surprise does not register on my face. Alastair is Lucian’s right hand man. Him being here means Lucian has already gotten wind of the situation.

 “What do you want?”

 “Just to clear things up. You see, my boss just wants to have his investment back.”

 “I don’t think Lucian ever had an investment that concerns the boys.” He clicks his tongue.

 “You’re wrong. You see…” he holds up a bean-shooter with a nice ivory grip, and a seal of Lucian’s Trouble Boys.

“Big brother Dean used to be Lucian’s best hustler. Racked up a lot of money hustling pool and cards. One of his best fighters too. But sadly, he lammed off. Boss is just trying to, well, compensate.”

 “Liar.”

 “You could ask him yourself. I’ll leave this…” he tosses the gun to me.

“Also, ask him how he got that pretty scar on his neck.” With that, the man dusts outta here.

 

**Notes for the Chapter:**

> And, that's it. I'm handing the reins over to Firefly124.
> 
> Hope you enjoyed this.


	6. Chapter 6

**Summary for the Chapter:**

> This week, on Fallen Angel, we get a glimpse into the past of Castiel's mysterious client.

**Notes for the Chapter:**

> Huge thanks to lotrspnfangirl for beta-reading this chapter! Finding the balance between "correct and readable English" and "Noir slang" is a new (fun! but new) challenge for me, and this chapter would be significantly less coherent without her help.

I don’t know if I was ever going to do what Cas said and just get some rest. But when Jess showed up to give me Sam’s schoolwork, that cinched it. I have the address of the motel that broad Ruby is supposedly shacked up in. I’ve got to use it.

Used to be, I’d’ve known where Lucian was putting up his songbirds. He mixed it up every once in awhile to keep the coppers on their toes, but when he found a place he liked, he tended to use it awhile. Not too close to the Caged Bird. Not too nice. Not too shabby.

When I pull up to the joint, I can see that the Dew Drop Inn is trying to be a classy place. Maybe it even was a few years ago. The peeling paint on the sign is a dead giveaway that it wasn’t anymore though.

I pull out the torn sheet of paper and read it again. If Crowley could be believed, Ruby’s in number four. Suddenly this all seems too easy. Would she just have Sammy kept in there? Wouldn’t Lucian kill them both? Did she take Sammy and run off somewhere?

Sitting in the parking lot isn’t going to get me any answers, so I grit my teeth and get out of the car. Soon as I knock on the door, she whips it open. So much for them making a run for it.

“Where is it?” she asks.

I look her up and down. Does she think I still… ? Nah.

“Where’s what?” I ask.

“The pizza that takes an hour to get here?” she asks, narrowing her eyes at me.

“You’re expecting someone to bring you pizza?” I ask. I don’t even know of a place around here that makes the stuff, much less brings it to you. “Well, it ain’t me.”

“No kidding, Dean,” she says. She crosses her arms over her chest and leans against the door jamb. “So what are you doing here?”

“Like you don’t know,” I say. “Where is he?”

“Where’s who?” she asks, like she’s bored already.

If she weren’t a dame, I’d’ve decked her by now. Still might, broad or not.

“Sam,” I say, gritting my teeth.

“Your brother’s a big boy, Dean,” she replies. “He doesn’t report to me, and he obviously doesn’t report to you.”

That feels like a kick to the gut. Since when couldn’t Sammy tell me stuff? She’s not wrong, though...

“You tellin’ me you don’t know?” I ask.

“I’m telling you it’s none of your business,” she says, straightening her stance. “If you really wanna know, though, you should probably go ask Alistair.”

For a second, I feel like someone turned my guts into an iceberg. Bad enough Sammy had been messing with this dame. Alistair? That was a whole other level of bad.

“Thanks,” I tell her.

“Don’t mention it. Ever,” she says. “And next time? Bring food.”

She slams the door in my face.

I get back in the car and bang my head against the steering wheel. 

“Sammy,” I groan, “what the hell have you gotten yourself into now?”

Alistair is Lucian’s main enforcer. The Trouble Boys report to Alistair, and he reports to Lucian. I used to report to Alistair, until a month ago. Some of the Trouble Boys hustle, like I used to. Some of them make book. Some of them see to it that welshers pay up, one way or another. That’s what Dad used to do. 

_I was the one found Dad after he kicked it. He was sitting at the kitchen table, head on his arms, half-empty bottle of hooch in hand. I didn’t try to wake him up; that never ended well. So, I let him sleep it off and went to go make sure Sammy was doing his homework. Sure enough, the kid was sitting on the bed with a book, paper, and pencil, glaring at it like that was going to get it done._

_“What’cha got there?” I asked._

_“Math,” he groaned._

_Not my favorite either, but I sat down and started trying to show him what was what._

_Halfway through a page of long division, a heavy fist banged on the door._

_“Open up, you piece of shit! I know you’ve got the money, John!”_

_“What money, Dean?” Sam asked._

_“Shh, Sammy.”_

_I knew Dad was doing some hinky stuff to keep this roof over our heads, didn’t know what was gonna happen if all that noise woke him up. Hell, I didn’t know if I was more scared of him or whoever was huffing and puffing out there._

_The door crashed open, and Sam almost shouted; I shoved my hand over his mouth. Dad had gone over the edge with the rams, or so I thought, but he could handle whatever came through that door. And if he couldn’t? Well, then it was down to me to keep Sammy safe. Hell if I knew what I’d do with anything that got past Dad, but I was gonna do it anyway. Best bet, though, was if they didn’t know we were even there._

_There was more crashing and swearing, but only that unfamiliar, whiny voice. It got right into your head like a needle through the ears. I couldn’t figure why Dad was being so quiet about it, but from the rest of the noise, it seemed he must’ve been getting his licks in._

_All of a sudden, it was quiet. I let my hand fall away from Sammy’s mouth, but I shushed him again anyway. Whatever just happened, Dad was gonna be in a rage. Footsteps came down the hall, and the kid glared at the door. When that door opened, we thought we were ready for the worst._

_We were so wrong._

_“Where is it?” The guy was skinny, but if he was here and Dad wasn’t, he must be packing more muscle than it looked like._

_“Where’s what?” Sam asked._

_“The money your daddy’s been hiding from me.” The guy sneered. “I mean, sure, obviously he drank most of it, but there’s gotta be some left.”_

_“Does it look like there’d be money hiding around here?” I demanded. Like we’d really be living in this dump if we had two pennies to rub together._

_“You’d better hope there is,” the guy said, “or your daddy won’t be the only one croaking today.”_

_I stood up and put myself between him and Sammy. He was lying about Dad. Had to be. He was just passed out was all._

_“Oh yeah?” I asked. “And how’s that gonna get you your money?”_

_He didn’t answer. Just looked me up and down till I wanted to crawl out of my skin._

_“What?” I demanded._

_“You’re right, kid,” he said at last. “Pretty boy like you is definitely worth more to me alive.”_

_Turned out I was right that I was worth more alive. Wished I wasn’t, but considering it also turned out Alistair was right about Dad being dead—already dead when Alistair got there, and probably already dead when I’d gotten home—I was gonna have to start bringing in some bread._

So I did. Right up until last month. And now Sammy’s not just lammed off with the canary, he’s mixed up with Alistair. 

“Son of a bitch.”

**Notes for the Chapter:**

> I hope you've enjoyed this week's ~~episode~~ chapter! Next week's installment will be from the lovely justholdingstill!


	7. Chapter 7

**Summary for the Chapter:**

> In which the plot subtly thickens, and Dean drags our hero to the 1940's version of a floating gay bar on a mysterious errand.

It’s the standard suspicious wife deal, the kind of case that case that comes across my desk just as regular and reliable as Tuesday nips at Monday’s heels. She thinks he’s out either chasing skirts or chasing pool-hall glory with the wage meant to put bread in their kid’s mouths, and nine times out of ten I’m sorry to tell her that she’s bang on. I could speak plain from the start, tell most of these broads not to waste their time, that it’s just the disease of darkest human nature in a city sick to its bowels with it, but I’ve learned by now it’s rare that she isn’t already certain of his motives by the time I’m slapping the glossy photos down in front of her.

Sometimes all they’re after is the solid proof, something tangible they can clutch in their balled-up fists, for better or for worse. For richer or for poorer, I provide. Mostly poorer. I’ve come to expect that, the same way I’ve come to expect the dull ache that crawls up my spine after an all-night stakeout, or the unmistakable thirst that comes on like clockwork after I’ve given away my third clean handkerchief of the day. 

Lot of crying in this business. I expect that too.

What I don’t expect is Dean Winchester, waiting for me on the doorstep of the brownstone where I keep a draughty attic apartment. I don’t recognize him right away, dressed as he is in a sharp gabardine suit, cutting quite a striking figure against the halo of sallow lamplight behind him. The phrase ‘tall drink of water’ steals across my mind, soft-footed, quick, and suddenly I’m sweating like a chilled glass left in the sun on the fourth of July. 

“I don’t recall giving you my home address,” I say. 

He shrugs, punctuating the gesture with an impish grin. Thunder rumbles in the distance. “A man wants to hear a train comin’ miles before it’s in sight, he puts his ear to the ground and listens. Simple enough.”  
That’s not altogether reassuring, but I’m not in the mood for riddles this side of the quittin’ bell.

“Tell me something - where’s a man like you get a fine cut of cloth like that, anyway?”

“Of the two of us, you’re supposed to be the detective here – why don’t you tell me?” That grin again, and they’ve called me hard-boiled in my time, but I’ll damned if there isn’t something akin to a blush fighting its way out from under my collar. My smart response dies a shameful death in my throat.

“I went around rattling some cages last night,” Dean says, cutting right to the heart of it, reaching into his pocket for his cigarette case. He offers one to me and even goes so far as to light it before his own, cupping it against the rising wind; and sure, maybe if they dragged me up on the charges I would cop to being distracted by the way the flare of his match dances in the green of his eyes, but not so distracted that I miss his hands trembling as he flicks it into the wet street. “Little bird sang me a song I wasn’t too fond of.” He licks his lips, presses them together. 

“Do I know the tune?”

“Rumour has it that Alistair’s got Sammy on his payroll,” he tells me after a beat. For a second, his face is obscured by the smoke he lets go on a world-weary sigh, and I lean on the pause just long enough to consider whether I should tell him about the kid’s visit last night. The pistol Alistair gave me is a cold reminder in my trench pocket, heavy against my thigh. Truth is, I could spill the beans and let him walk away now, leave him to deal with his own mess the way he surely should, but there’s something about this one I just can’t shake off even though I know he’s given me nothing like the whole story. They say that curiosity killed the cat, but I’m willing to bet all that talk about nine lives ain’t just useless jawing either.

Yeah, there’s something about this one.

“I’ve heard the name,” I allow. I have. Back rooms and basements all over town, never louder than a whisper, voices shaking only half as fierce Dean’s hands had just a moment ago. “Used to run with the Princes of Hell. Nasty sons of bitches – even nastier than Lucian’s mooks. Or so I’m told.”

“Would you look at that?” Dean says to the sky, sidestepping my unspoken question all soft-like. “I’d say heaven’s about to open up on us, here, Cas.” He fingers the thin silver rope of his scar, stretching from ear to ear in some unholy echo of a smile; I can’t help but wonder if it pains him when the rain’s coming, the way my great aunt Amara claimed her knees used to ache in premonition. “Listen, you wanna get out of here? I’ve could use a stiff one, and I might know a place in this town even you ain’t laid eyes on yet.”

“Doubtful,” I scoff, but I’m not exactly protesting when he steps down to the curb and shakes his head at my bucket of bolts leaking oil onto the pavement, kicking the tires like the state of it’s done him a wrong that’s real personal. He looks back over his shoulder at me.

“Motor city’s finest,” he says, deadpan. “We’re taking mine this time.”

It’s not until we’re in the car and winding our way through a warren of alleyways I barely recognize that he speaks again, so quiet I think he’s only talking to himself at first. “If you're really as good as Bobby said, then you'll understand what I mean when I say my family’s been singing those Perdition Street blues long enough. I’ll be buying myself a one-way ticket to hell with my own pocket money before that no-good belly draggin’ scum gets his rotten teeth in Sammy any deeper than he already has. I know what I've gotta do, Cas. I know what I've got to do.” 

 

Time was, I thought I had at least a passing acquaintance with all the nooks and crannies this town had to offer when it came to the rarified flavours of jazz and hooch and sin. 

Then again, I never rode out to the far eastern edge of the dockyards before, climbed down a ladder rustier than my bed springs, and helped steer the waiting rowboat through a downpour into the heart of the harbour’s mist, watching an old barge-cum-nightclub materialize out of the gloom. I never thought to, but maybe that’s what a lifetime of keeping your toes in line and your nose a little too clean will get you – a lack of imagination. Exactly what the force had wanted me for, even decorated me for, at least ‘til it turned out I couldn’t imagine away all the grease I’d seen cross palms, the stink of disillusion and corruption sunk so deep in the system that it had flies circling the mayor’s office. 

But I digress.

Dean had called it “The Bunker” on the way over, so maybe I was expecting something a little more subdued, a little more subterranean. Anything but...this.The wild, cacophonous wail of a sax is already assaulting our ears before we get on deck, and inside I’m not prepared for the glittering crush of bodies, the perfume, the smoke, the riotous colour and light of it all. It’s the most liberated scene I’ve laid eyes on in a long while, and I’m just slack-jawed there by the door until Dean grabs me by the sleeve and hauls me along to a mirror-lined booth a little further away from the dance floor. 

“Someone I gotta see, Cas. It’s important. I hope you don’t mind,” he tells me, leaning in as he pitches his voice to be heard over the ruckus. Up close, I wonder how I never noticed the tawny spray of freckles over his nose and forehead before. 

There’s a woman in red silk already waiting in the booth. She’s a hot little number all right, legs for days, looking both bored and mischievous with an enormous scarlet begonia pinned behind her ear. I try not to waste too much time wondering how Dean knows her. A face like his, I have a hard time thinking he’s ever hard-pressed for the company of a warm body, no matter his…preferences. 

“Winchester,” she says, nodding curtly. “’Bout time.”

Dean rolls his eyes. “Stow it, _Celeste_. There’s someone I’d like you to meet.”

“Charmed, I’m sure, blue eyes,” she drawls, motioning at us to join her. “They in the habit of handing out names, where you’re from?”

“Castiel Novak, P.I. It’s a pleasure to make your acquaintance, Celeste.” 

“Just between you and me, mister? That’s not my real name. Dean here thinks he’s a hoot, but you can call me Charlie. Charlie Bradbury,” she says, dropping the act. She slaps her palm into mine with a wink and a frankness that makes me like her immediately, despite my better judgement.

“A few fingers of your best for these two scoundrels, and another martini for me, dollface. Extra dirty, if you don’t mind.” Charlie dishes out another wink to the waitress who's appeared to take our orders, and she colors prettily as she turns to go and fetch our drinks. The kid's got these long, knock-em-dead eyelashes that she keeps fluttering in Charlie’s direction with such focused intent I’m surprised the redhead can’t feel the gaze lingering over her skin like a light breeze. 

Least, I would be surprised, if the redhead in question hadn’t coincidentally chosen the only seat at the table with a peripheral view of the bar; she swirls the olive in her glass in contemplative circles as she talks, and even though she keeps up a lively conversation with Dean, I catch her stealing long looks at the sleek-haired dame in suspenders and khaki trousers behind the counter, slinging cocktails with easy grace. 

Dirty martini, indeed.

"You're terrible, Charles," Dean scolds, kicking her under the table. "You gotta stop leading Gilda on like that. You know it don't ever work for us to get mixed up with civilians."

I get the sense that I’m not supposed to notice the slip, but then again, men like me don’t get into this line of work not to notice things. I might not be the slickest schmuck around, but I flatter myself that what I lack in social prowess, I make up in the skills of observation that have become my bread and butter. And by the time Charlie leans in to press a friendly smack of a kiss to Dean’s cheek, surreptitiously slipping a small blue envelope into his breast pocket before sashaying off to take a powder, I know I haven’t missed my ticket. It’s beginning to dawn on me that I might not be going hungry, tonight, in more ways than one. 

That is, until Dean leans forward on his elbows, all feverish intensity, and asks outta nowhere: "So...the name Azazel mean anything to you?"

**Notes for the Chapter:**

> *tiptoes back in to add author's notes* 
> 
> Hi folks, I hope you enjoy the latest installment of _Fallen Angel_...woo, I finished something!
> 
> This was a ton of fun to write, and the hardest part was limiting my verbose ass to under 2k words because I had so many ideas for where this thing could go. I am also probably gonna be busting out a noir fic in future - once you get the rhythm, it's super addicting. I focused a little less on slang, and a little more on trying to create an atmospheric noir mood; I watched _Gilda_ twice in a row to get the feel, and listened to [this](https://www.youtube.com/watch?v=WDippeD3pj8&t=166s&list=FLgwSDBeUoKOYtDh0KgKHjMg&index=9) pretty much nonstop. XD
> 
> I _love_ how all of the previous participants brought their own unique styles and interpretations to the thing, and I can't wait to see where [MaskofCognito](https://archiveofourown.org/users/MaskofCognito/pseuds/MaskofCognito) takes it next!


	8. Chapter 8

**Notes for the Chapter:**

> Since Nadia had the fantastic idea to include the not so commonly used terms in the end-notes, I've done the same.   
> Sorry about being a day late, but here's the chapter:

Charlie stares Dean down, hunches over the table, and whisper-yells, “Azazel!? Are you kidding me right now? I get that you were a part of Lucian’s run-around under Alastair, but now you’re just hunting for trouble, aren’t you?”

I am puzzled. “Why does that name sound so familiar?” 

Dean leans a little closer to my side. “He used to work under Lucian before they split. It was shortly before I joined. And from the rumors, it was a nasty affair.”

We both turn back to the broad before us. She’s anxious where moment’s ago she was fine. 

“Look. I know you, Winchester. You don’t have a meter for danger—or at least if you do, you sure as hell ignore it. But Alistair and Lucian are bad enough to be already mixed up with.” She pauses to down her drink. “Azazel was Lucian’s prodigy. But things went sour between them. There was almost a full out civil war before they went separate ways.”

“And if the rumors are to be trusted, they have a vendetta against each other,” Dean adds. 

Charlie looks Dean dead in the eye. “That’s no rumor. It’s the truth. If ever the opportunity is presented, one will ruthlessly prey on the other’s weakness.”

Dean straightens. I am intensely curious as to why he brought up such a high profile name. In fact, I haven’t a clue as to what I’m doing here. After Sam’s visit to the office, it seems to me that he  _ wants _ to be in the shady business. Dean doesn’t like it.

I down the hooch in front of me. An air of danger I haven’t felt in a long time tickles at my intuitive senses. The only words that could express this feeling: we’ve gotten into some deep shit. I just hope we can figure out how to crawl out when the time is right. 

The conversation between the three of us turns light, and we end up drinking more than I anticipated. 

My head hurts something fierce and my eyes won’t open. It feels as though I’ve been run through the mill and back. I must have drunk too much last night. 

The bed beneath me is unforgiving. In fact, I wonder if it’s a bed at all. It’s too hard. I know that sounds ridiculous, but I can’t feel any springs, and there isn’t even a slight bounce. Only hardness. And cold.

I struggle to open my eyes, but the moment light cracks through my eyelids the world starts spinning. “Ung,” is the only thing I can get out. 

“Glad you can finally join us, Mr. Novak.” Clear, slow, and slightly raspy words bounce around the air. The voice is not one I recognize. 

I hurry to rid my eyes of any crust and force them open. The lighting is harsh and blinding, and it takes me a moment to focus, but the sky I can see beyond the manmade illumination is still dark. I look away to assess my whereabouts.

Warehouse. Or something damn close to it. I smell salt, and I hear birds and lapping water. Maybe we are still on the island? 

Dean is beside me, but he’s unconscious. I wonder how long the man before us has been waiting for one of us to wake up. 

“Do you know who I am?” The voice returns, still in that unhurried tone.

I face its origin. The lights are bright and blinding. I blink away tears as I force myself to adjust and bear the discomfort. I can see a figure basked in the headlights and shadow. He seems of average height and build, nothing extraordinary. Nothing besides the way he holds himself and projects some sort of invisible power.

I  crab a guess on the proceedings of our night. “You wouldn’t happen to be Azazel, would you?”

“Very good, Mr. Novak. Very good.” 

I wince. The stories from earlier were not ones I want to personally corroborate, and definitely not so soon. But I still wonder why we were taken to greet the legend personally and what business he has with us.

“Excuse me, but why are we here?” I’m exhausted and feel as if a train car ran over me. I don’t remember drinking enough to feel this shitty, but I suspect it wasn’t the hooch that led to my current condition. My patience is growing thin, and my irritation is starting to show.

“A little testy, are we? I wouldn’t be too rash. You’re outnumbered, outgunned, and not up to your usual physical prowess.”

I cough and immediately regret it as my ribs twinge. “Ow, shit…” 

The other men are quiet, more patient than I. I pause only to catch my breath and still the pain. “Where the hell are we? And what, exactly, do you want with us?”

“Don’t you mean what do  _ you _ want with  _ me _ ,  shamus ? I’ve got snitches, you see. Heard some people have been throwing my name about, tonight. Made me mighty curious. What kind of sane folks would go snooping around about me? Only two kinds: people lookin’ for work, or people lookin’ for a watery grave.”

I laugh to myself. 

“Well, you’re asking the wrong guy.” I shake my head. “I haven’t a clue what he’s scheming. The conked-out pretty boy over there is the one with all the plans this time ‘round.”

I  _ wish _ I knew the plan. I hate making my charge take the blame, but I have no answers for this high pillow hoodlum. Seems like the Winchesters have me along for the ride rather than letting me do my job. Though, to be fair, I have no idea how to go about it if Sam doesn’t want to be brought home.

I look around the room. I see two shadows of men and their tommy guns on either side of Azazel now that my eyes aren’t stinging so severely.  Brunos . Dean, boxes, crates, concrete, and metal are the only other things I take in as I whip my head around. “Speaking of, I don’t see the dame we were with earlier. What’s the deal, huh?”

He laughs sardonically. “You  _ want _ me to put the works on a dame?” Azazel turns to address his men before facing me again. “You hear this chump, boys? This lug thinks I hit women for sick pleasure or some bullshit.”

“No. Just wondering if you’re playing favorites with us.”

“Ms. Bradbury is a rat for hire. She takes no sides. Stays clean. Only speaks up when visited and for a fee. It’s how she gets by, and she gets by well.”

“But what I witnessed last night—she didn’t fit the type to spill the beans on Dean. Seemed to me they were pretty close friends.”

“Funny thing”—he shrugs and steps closer—“the idea of friendship is often fickle when you are offered only two alternatives:  lead poisoning or  spinach . Not that it was her choice. We made sure she spoke.”

Dean stirs next to me. “Oh, man. What the hell happened?” It takes him a moment to understand the circumstances. “Aw, fuck. Azazel, right?”

“Bingo,” I say. “And he wants to know why you were asking about him.”

Dean looks to me and then blocks the lights with his hand as he attempts to look at Azazel when addressing him. “Right. I didn’t expect to get a chance to talk to you.”

He stands up and dusts debris off his clothes before offering me a hand. I take a quick glance toward Azazel to see his reaction, just in case he intends to keep us low to the ground for the further effect of whatever power he holds over us. He seems unperturbed, so I grasp Dean’s arm, pull myself up, and straighten myself out. 

“Lucian has my brother under some false pretenses. Or at least I think so.” To my surprise, Dean starts to tell Azazel everything. I’m now intensely curious about his plot. “I’m pretty certain Sammy believes he’s doing right by me. I used to be part of Lucian’s faction. I left the gang a month ago, and he’s been acting weird ever since. He caught himself up with The Caged Bird broad, Ruby. Her talons are sunk in, and she’s bad fucking news.

“I guess... I’m asking for help, Azazel. I know you and Lucian have a never-ending feud and I’m looking to expose some of his secrets if you can help get Sammy out. I can’t do it. I’ve tried and failed.” Dean looks down at his hands, showing his uncertainty. “I… I don’t know if asking another mobster is really going to make the situation better, but I’ve got to try what I can to change the tides. I don’t like it. It’s not right for Sammy. So, can you help me?”

**Notes for the Chapter:**

> **Crab** — figure out  
>  **Shamus** — (private) detective  
>  **Bruno** — tough guy, enforcer  
>  **Lead Poisoning** — to be shot  
>  **Spinach** — money  
>  Resources from mistkatonic.org.
> 
> I hope you enjoyed it, and I cannot wait to see what [LegendsofSnark](/users/LegendsofSnark) has in store for us next week!


	9. Chapter 9

I can't help but stare at Dean as he asks for help, help from the man that currently has us held in this warehouse like it’s a Calaboose. I knew he would do anything for his brother, who wouldn't, but asking  _ this _ man for help was another thing. 

 

“Dean…” I try to whisper, voice low, but Azazel chuckles and I know he can hear me. The man stands in front of us and runs a hand down my cheek. I flinch away and that only causes him to laugh harder. 

 

“I'm sorry. But whatever–” Dean swallows harshly, eyes flicking to look at me. . His eyes are filled with sadness and hurt.  I can't help the small twinge of guilt that eats away at me when I think about trying to get us out of here and have Azazel locked away. “–whatever bond, friendship, we have, mine with Sammy is stronger. He’s my  _ brother _ , and I owe to to him to get him back. He deserves that much, ‘specially when it was my stupid-ass decisions that got him into this mess in the first place.” Dean turns back to Azazel and says, “I’m willing to do anything to get my brother back. That is, if you’re willing to help me.” 

Azazel grins, wrapping his arms around Dean's shoulders and pulling him close against his chest. There's a kiss placed on his head that leaves me feeling a little green around the gills as I watch it. “I would be more than willing to help you with anything. That is, if you’ll do whatever it takes. I mean, there will be things that I ask of you and I need to know that you're willing to take those chances.” 

 

I step forward, grabbing Dean's hand and pulling him away from Azazel. “You ain't gotta do this, Dean. I can help you. You don't need to turn to this…  _ criminal.  _ If you get wrapped up in his business. I won't be able to help you out of the mess. You're gonna be on your own after that.” 

 

Dean lets go of my hand. His eyes are fixated on Azazel and there’s something inside of them that I can’t read, something dark, and I’m worried. 

 

I didn't want him to go down that road – I couldn’t let him.

 

“I'll be okay. You don’t know half the shit I got up to before you came along. If I get into any trouble here, I can take care of myself. You ain't gotta worry about that. Breeze off, Cas.” 

 

I know that I'm gonna worry. Dean doesn't know what's gonna happen if he goes down this road. 

 

                                           ×

 

When I get back to my apartment I plop down on the couch and prop my feet against the coffee table. My life had taken a turn since meeting Dean Winchester, and he had sent me in a whirlwind that I wasn't prepared for. But I also would do anything for him, to save him.

  
  


There's a knock on the door. I glance at it for a few seconds, before deciding that whoever it was, they could always come back later, after I had decided what to do about the situation with Dean. I didn't have any clients at the moment, and the ones I’d had before knew not to visit me at home. 

 

The knocking continues, and it's persistent. With a huff, I stand up and walk over to the door. When I open it, it's the last person I had expected to see. 

 

Jess Moore. 

 

“Ms. Moore? What are you doing here?” 

 

She shakes her head and I can see the tears streaming down her face. 

 

“I know that Dean said that you were helping to get Sam back and that's great and all but it's been a while since we heard anything and I'm just worried about him and today a bunch of gangsters showed up at my mother's apartment looking for me.” 

 

I wrap my arms around her, pulling her inside of the apartment. 

 

“The gangsters, did they say who they were working for?” 

 

Jess shakes her head. “All I know is that my mother said that they were looking for Dean. And I don't know what's going on! I'm scared. I want Sam back and I just—" 

 

She lets out another sob, and I sit her on the couch and get her a handkerchief to wipe her tears. 

 

Normally Castiel’s tongue wouldn’t be as loose, but feels bad for the poor dame. “Listen to me, Ms. Moore. Dean made a deal with Azazel to get Sam back. Those could have been his lackeys or they could have been someone else's. But all I know is that for a while you should lay low. If you need to, leave town.” 

 

“Mr. Novak?” 

 

I give her my best smile. “All of this will be over soon, Ms. Moore. I can guarantee you that.” 


	10. Chapter 10

**Notes for the Chapter:**

> This chapter was rather difficult for me to write, but I quite like how it turned out. Enjoy!
> 
> A heapings of thanks goes out to [Nadia](https://hartlessfiction.tumblr.com/) for beta-ing - this chapter would be completely different (and not very good) without her.

The look on Cas’ face when I made the deal almost has me regretting it. _Almost_. But I’ve been looking after my brother for so long that I–I don’t know how to do anything else.

So here I am, walking down the street to my run down apartment, too holed up in my thoughts to notice my door’s unlocked—swinging open—until I’m a foot in front of it. Dread curls tight and low in my stomach and I’m immediately on edge, one hand snapping to the bean-shooter tucked in the folds of my jacket. I creep forward slowly.

A small part of myself hopes it’s Sammy, come home, but knowing my shitty luck, it’s more likely Alastair waiting to plant a bullet in my skull.

The door creaks as I step inside. Footsteps echo on the dirty kitchen tiles. I swing around, finger on the trigger jumping like the vein in my neck— “Charlie?”

“Took ya long enough,” she says, a smile twirking at the corner of her lips. There’s a blotchy, red-brown bruise going from around her eye to the edge of her cheek.

I don’t lower my gun.

“Don’t blow your wig, pally,” Charlie says sarcastically. “Or I might think you’re actually happy to see me.”

“I only caught the tail end of Azazel’s comment, but it seems that you’ve turned on me.” My voice is cold, unyielding. “You know, in all the years I’ve known you, I never took you for a grifter.”

“I’m sorry I did that,” she says, not meeting my eyes. My hand is sweaty around the handle of my gun. It pains me to have it trained on my old friend, but I hold steady. “But only because I had no choice,” she says, her hand gingerly touching her bruise, “and I knew Azazel wouldn’t hurt you, because he needed you. But I’m going to make it right by you, Dean, I promise you that.”

I could question Charlie furthur, but I’m too damn tired. And if I can’t trust Charlie, I can’t trust anyone. I ease the gun back into my jacket. “I made a deal with Azazel,” I say. Hadn’t even been meaning to say that—the words just slipped out like butter.

“Son of a bitch,” Charlie mutters, scowling. And yeah, I deserve that. “What’s the deal?”

“Azazel helps me get Sam, then I help him do a job. Or two.”

Charlie swears some more. “That’s the dumbest shit you’ve pulled yet, Winchester.”

“You and me both.”

“Well, ah, I got me some happy news for ya. You know, I didn’t spend all the time you were gone just getting my ass beat and waiting around for you. I may have spoken to a little canary that said she was tired of singing for her boss. And she may have given me the location of Lucian’s new main base.”

It takes a hot second for me to catch Charlie’s meaning, but once I do, I break out in a grin. “Are you saying you know where Lucian is, where Sam probably is?”

“I’d bet a date with Gilda that that’s where they are.”

I swing forward, pulling Charlie into a tight hug. “Thank you, Charles.” I say as I plant a friendly kiss on the top of her head. “You’re really becoming more and more of the little sister I never wanted.”

“Aww, don’t go getting soft on me, Winchester.”

“No promises,” I mumble as I pull away.

The smile soon drops from Charlie’s face. “You know, Azazel’s not gonna be happy you no longer need him.”

“Yeah, well, screw him,” I say. “As long as I have you and Sam by my side, I can take on anything.” A small flare of hope sparks in my chest. I’ve been so damn tired for so long that it catches me off guard. I can almost see the light at the end of the tunnel. And once this is all said and done, if I can take Cas out for a drink, well, that’s even better. “And…” I say slow, careful, “maybe Cas too, if he’ll forgive me.”

“Knowing how much he seemed to like you at the Bunker, my cabbage’s on yes.”

 

I don’t really know how to comfort Ms. Moore—hugs are as foreign to me as having a life free of danger—and I find myself uncomfortably patting her back when the sound of footsteps erupts on the other side of the door, and Alastair barges in, two henchmen on his heels.

My surprise chokes me and all I’m able to sputter out is, “How did you find me?”

“Did you think I wouldn't have a few of the Trouble Boys keeping tabs on the skirt here,” he says, nodding to Jess. “It was _all_ too easy to follow her here.”

I spare a glance at Jess. Her face constricted in fear and my green’s on that she didn’t know about any of this. An innocent like her wouldn’t know what a tail looked like if you pointed it out to them.

“Boss isn’t too happy with you now,” Alastair goes on. “He was willing to turn a blind eye to what you’s were doing, but after you and pretty boy Dean got in a little tangle with Azazel, _well_ , that Lucian can’t stand for. ‘Specially not after all the hospitality he’s shown yah. So he wants the nancy boy dead. Now, word on the streets is that you two have been… gettin’ real close,” he pauses to sneer. “Seems like you’ll make the perfect bait.”

I force myself not to react to Alastair’s accusations, not confirming or denying how close Dean and I have become, ‘cause letting that out wouldn’t help nothing. The weight of the situation lays heavily on my shoulders and I can’t stop my eyes from darting to the henchmen by the door. They’re two lumbering, bears of men, and if Jess wasn’t here—a civilian that could be hurt in the crossfire—I’d’ve tried to take them on myself, would’a gone down fighting. Instead I lower my eyes and say, “I’ll go with you, just, don’t hurt the dame. She’s got nothing to do with this.”

“Oh, she’s got everything to do with this.”

I stare at him, eyebrows furrowing. “What are you on about?”

He tuts. “You don’t know nothin’, do you, boy? Jess? Is Lucian’s kid. Now, she was tryin’a do right, stick by her mother, not get wrapped up in this mob business, but there’s never really any running from it. And poor Sammy, he tried to get into her daddy’s good graces by becoming one of his Trouble Boys. Doesn't seem to be working out for him,” Alastair’s cackle at that chills me to the bone. “Now, I think her Lucian’ll be expecting you two, so let’s go.”

As one of his henchmen roughly pulls me to my feet, I turn an eye on Jess. “Is this true. Is Lucian your father?” Her silence is answer enough. “Dammit.”

**Notes for the Chapter:**

> You're welcome for the plot twist out of nowhere, and with practically no backing to it.
> 
> Up next is the lovely supernatural9917fic!


	11. Chapter 11

**Notes for the Chapter:**

> Thanks to smudgythoughts for looking over this chapter and making some helpful suggestions :) This was fun, and I hope I haven't made too difficult a set up for uncelestial next week!

"I'm sorry, Mr. Novak," Jess says softly, looking contrite. "I didn't mean…"

"Don't worry about it," I tell her with as much of a smile as I can muster. "Shall we, gentlemen?" The goons apparently can't be sweet-talked, and they're not exactly gentle when they shove me out the door.

"Leave him alone." The voice belongs to Jess, but there's a new steel in it that makes everyone stop and turn to her.

The younger-looking henchman laughs harshly. "Or what, sweetheart?"

Jess walks right over and looks the dumb mug in the eye. Yeah, she's definitely Lucian's kid. "Mr. Novak is my friend. You'll treat him with respect, or I will tell my father."

"You do that, dollface," the guy says mockingly. "Come on, let's go." I get manhandled to the waiting car, but at least Jess is treated with a bit more politeness by Alastair. We both end up in the backseat, Alastair squeezing Jess into the middle seat as he climbs in after her.

Jess turns to me and fixes me with a determined look. "I really am sorry, Mr. Novak. But I _will_ make this right, don't worry." Maybe I've taken one too many knocks to the head, but I can't help but believe her.

The rest of the trip to The Caged Bird passes in silence, but my mind's racing. I don't doubt Jess can hold her own, especially since Lucian is her father, so I let myself stew on the problem of Dean. His game with Azazel is dangerous, but I know he's not some dizzy kid- he's gotta have some bigger plan.

I hope.

All I can really do is buy him some time, and maybe keep Lucian's Trouble Boys off him until he can pull off whatever hare-brained scheme he's running. An idea starts to form, and by the time we get to the club, I've got the beginnings of a plan.

Jess and I get taken around the back and marched straight into a plush office, where Lucian himself is sitting in a large wingback chair, surrounded by another couple of goons. His sandy hair is Pomaded to an inch of its life, and his three-piece suit is clearly expensive, but his pale blue eyes are surprisingly soft when he looks at his kid.

"Princess," he says gently. "It's good to see you."

"Daddy," Jess replies tersely. She does not seem as happy to see him. "I don't know who the new Bruno is, but he was very disrespectful to my friend Mr. Novak." She crosses her arms and glares at said Bruno. "And to me."

Lucian turns to the poor sap with a look that I definitely wouldn't want to be on the other end of.

"Is this true, Gerald?"

Gerald looks a lot less cocky all of a sudden. "I… I thought we were supposed to rough up Novak, sir."

"That was before I knew that Mr. Novak was a friend of my princess," Lucian explains as if to an idiot child. "Mr. Novak, please have a seat. Can I offer you anything?"

"No thank you," I reply politely, shaking loose from Gerald's grip and sitting down as casually as I can. "May I ask why we've been brought here so… unceremoniously?"

Lucian leans forward to rest his elbows on the desk and steeples his fingers. I think his smile is meant to be friendly, but he gives me the heebie jeebies.

"I've been made aware of your… connection with Dean Winchester, and the little _incident_ with Azazel. Dean is a very ungrateful young man, and I need to have a strong word with him. I think with his brother and his… _friend_ here, not to mention my baby girl, there's no chance that rube won't turn up."

Jess, who still hasn't taken a seat, turns a look of utter rage at her pops. "You're using me as _bait_?" she yells, and Lucian actually flinches.

"Of course not, Princess. I just mean that Dean won't try anything rash if there's a lady present. I would never do anything to hurt you, sweetheart."

"Oh really?" she asks incredulously. "And what do you call abandoning my mother for that floozy Lilith?"

This is a juicy bit of family drama, and the gumshoe in me really wants to hear more, but Lucian is spared from having to reply by the entrance of another goon, this one with Sam Winchester in tow. The smile when he sees Jess is quickly replaced by shock when she storms over and slaps him hard across the face.

"Next time you want to impress me, bring me flowers. I don't go with Trouble Boys."

Sam's face crumples. "But Ruby said-" That earns him a slap across the other cheek. I almost start to feel bad for the poor kid.

"Do I look like the kind of girl who would tell a doxy like that any of my secrets?" Sam has the decency to look abashed, so Jess rounds her attention back on her father. "Daddy, you need to let Sam go. You know he's not cut out for this."

"I can't do that, Princess. Not until I've strung up his brother."

"That would be a particularly stupid thing to do," I chime in, finally sensing an opportunity to get a word in edgewise. Lucian looks at me with surprise, like he'd forgotten I was still here.

"And why is that, Mr. Novak? Are you going to avenge him?" He laughs at his own joke, and the mooks around him snigger along with him.

"I simply mean that it would be a poor show of gratitude for Dean's bravery in delivering Azazel to you on a silver platter," I say coolly, inspecting my fingernails to give off an air of nonchalance.

"I'm not sure I follow you, Spade."

Why do people keep calling me that? "Surely you're wise to his game. First, he quits working for you, gives the impression that he's turned on you. Then he goes around, asking about Azazel, not exactly in a subtle way neither, and bam- suddenly he's got an audience with the goose himself, a spot in his circle, and the perfect excuse to come after you. He makes a plan, talks Azazel into coming in on the attack on your turf… Do you see the picture I'm painting here?"

I can see the cogs turning in Lucian's mind, and I spot the second he gets it. That unpleasant smile grows wide, and he throws himself back in his chair with a laugh. "That's a nice bedtime story, Mr. Novak. But how would Dean get word to me so we'd be prepared for the attack?"

I roll my eyes heavenward and tilt my head towards Sam. "The disappearance. Hiring me allegedly to look for him. It was all a ruse. Sam's the inside man, I would deliver the message from Dean when I 'found Sam' during my investigation." I used my fingers to indicate the quotation marks, making it clear that I was being facetious. "Unfortunately, this little shindig has thrown a monkey wrench into the works."

Lucian turns to Sam, who I hope and pray isn't a complete sap and has caught on to the string. "Is this true, Sam? Are you and your brother really running a grift on Azazel for my sake?"

Sam hangs his head, and for a minute I think we're cooked. "I'm sorry, sir, I should have told you, but Dean said you shouldn't find out until the last minute, in case there was a canary in your organisation singing to Azazel." Hallelujah and praise be to Chuck, owner of the liquor store I'm going to drink assuming I survive this hootenanny.

Lucian looks smug, presumably thinking about the loyalty he's inspired in the Winchester boys, and finally he turns to me. "Very well, Mr. Novak. I'll have Viggo take you back to your humble abode to continue your little plot. But let me warn you now- if you double-cross me, I'll be replacing that grubby trenchcoat with a nice Chicago overcoat. Capisce?"

"Yeah, I capisce." With a nod to Sam and Jess, I stand up to leave, but the door busts open before I can get anywhere. Rats- it's Dean and Charlie, and they're all guns a-blazing. "Dean!" I shout, hoping to get his attention before he opens his trap and ruins everything.

"Cas! Are you all right?" He's got his revolver pointed at Lucian, seemingly unconcerned at the half-dozen bean-shooters aimed at him.

"Dean, I'm fine. Don't worry, I've told Lucian all about your plan to deliver Azazel." I can only hope that Dean is as swift on the uptake as his younger brother.

"My plan?" he asks, and my stomach drops to my feet. Then Charlie smacks him upside the head.

"No sense playing the boob now, Dean," she says. "If Lucian knows the plan, it won't protect Cas to pretend he's not in on it." She turns to me with a gleam in her eye. "Just how much did you tell him, Cas?"

"I laid it all out, right from Dean leaving the crew and pretending to join Azazel's gang, hiring me to pretend to find Sam so I could be the messenger, and Dean leading Azazel here for Lucian's boys to take care of. I left you out of it, I thought you might want to maintain your reputation for neutrality."

"You're a peach and a half, Cas," she says warmly, "but it's OK. After Azazel roughed me up, I'm not interested in playing nice with him."

That's when I notice the bruise on her face. She's covered it up with powder and rouge, but it's still fresh enough to be noticeable. I don't like cats who beat on dames, and judging by his murderous expression, neither does Dean.

"He'll pay for that, Charlie, don't you worry," he says chivalrously.

"Well this is all delightful," Lucian interrupts, "but can I ask why you've come barging into my office armed to the teeth if you're on my side?"

"Obviously it was not part of the plan for me to be taken from my home at the point of a gun," I say dryly. "I can only assume that Dean feared our scheme was blown and came to rescue me."

"That's right," Dean confirms. "But I can see we're all still pals, so I'll just put this away." He holsters his rod, and after a signal from their boss, the goons do the same.

"Well, now that's settled," I say, taking my seat again. "It looks like we'll be needing a new plan." We all eye each other for a minute, and then Charlie breaks the silence with a snap of her fingers.

"I've got just the thing!"


	12. Chapter 12

**Notes for the Chapter:**

> Thank you so much to JessJessTheBest for be my beta for this!! It was really fun to work on this and I'm excited to see how it wraps up!

Halfway through the explanation of Charlie’s plan to draw Azazel out, Lucian started cackling like he’d just escaped from the loony bin. I fought not to cringe at the sound. Maybe I should have been used to it after spending my time watching Alistair lay-in to those on his rack. After doing my fair share of making clammy bodies open their yaps and spill the info the boss wanted. I had to keep reminding myself it wasn’t normal. Even now. 

 

I still had the same thing to keep me grounded. As pissed as I was with my brother, he was keeping me afloat. Or at least he had been until this stunt. What the hell did he think would happen? I’d be glad if I dragged the two of us outta this alive, let alone the sorry saps we’d dragged in with us. 

 

I couldn’t even look at Cas after confirming he was safe. Guilt curled around my throat, squeezing just like the blade of a knife. I had the urge to itch my scar, but kept my hands curled at my sides. I tuned out the conversation around me, solely focused on my lifeboat. Or was he the one dragging me under this time? It didn’t matter. I’d do anything to protect Sam, even if it cost me my own life. I’d made a deal with that downright demon Azazel, hadn’t I?

 

But I couldn’t ignore the fact he was the one who ran off in the first place. My anger simmered on the surface of my face. I kept my eyes on it’s source. Communicating silently in the way only we could. His eyes were big and pleading, mouth worrying itself sore. It went back and forth between us. 

 

_ I’m sorry.  _ Sam’s eyes would say.

 

_ How could you?  _ Mine would snap.

 

_ I’m sorry. _

 

_ You’re in so much trouble Sammy. _

 

I still gave him something, though. We could have the rest of this battle when the dust settled. The slightest tilt of my head downward. A nod of acknowledgement. A signal.  _ Trust me. _

 

We finished out our silent conversation just before the voices in the room reached a lull. Charlie must have finished spilling out her plan. Lucian was grinning like a true shark. All teeth.

 

“Never knew a dame to have a brain like yours, dollface.” The crook said, his voice oily and slick and just as nasty as he was. Jess coughed loudly, face screwed up tight in disgust. Seems like her daddy went and forgot she was in the room. I would of laughed if it wouldn’t lose me my head.

 

“I think it’s time you went on home, Princess. I’ve got business.”

 

“But—”

 

“ _ Now. _ ” 

 

I felt shivers up my spine. It was the first time he’d actually used force in his voice. The man was every bit as imposing and dangerous as his reputation. And to his own daughter no less? Jess was led out of the room without another peep. Seemed we were thinking the same thing.

 

Lucian turned his eyes back on our rag-tag group. My limbs felt stiff as boards, my whole body weighed down like I’d already been fitted for a pair of cement shoes. Which I would be if any part of Charlie’s  _ real _ plan went wrong. 

 

_ “That’s batty! Crazy! You’re crazy!” I don’t think I’d ever yelled at Charlie. I guess there’s a first time for everything. _

 

_ “Aw, Dean you flatter me.” The redhead said with a sarcastic bat of her lashes. _

 

_ “I’m serious. How the hell do you expect to pull this off?” I rubbed my forehead. As if it would wake me from this nightmare.  _

 

_ “With flair.” _

 

_ Charlie sat next to me on the couch, hand curling around my shoulder. Offering a comfort I rarely got from people. But Charlie was one of a kind. _

 

_ “Look, Dean, I know it’s scary. I know there’s a million ways this could go wrong. But what choice do we have?” She was right. We were already grasping at straws. “We’ll get your darling sleuth, we’ll get Bobby on the ready, we’ll get the friend I told you about. Have us an all out rumpus. Put a hole in the two biggest bastards in town, and get their goons in a slammer all in one fell swoop.” _

 

_ “Still crazy. And Cas’ not my—” _

 

_ The look she gave me said it all. Maybe I’d been too obvious about the glances I sent Cas’s way.  _

 

_ “Whatever he is, I can’t involve him. Or you. Or anyone. It’s my fight.” I was firm, standing up like I was about to be drafted into war. Which in a way, I was. But Charlie looked at me with the softest smile on her lips, a distant pain in her eyes. _

 

_ “Sometimes you don’t get to choose who’ll follow you into hell. You underestimate how much people care about you, Dean.” _

 

_ I didn’t have anything to say to that. I was out of options. Better to follow a plan then have her running in guns blazing after me, as she was so clearly ready to do. I’d gotten Charlie out of working for one of Lucian’s enemies back in the day, sure –  helped her set up her own gig elsewhere. But I didn’t deserve this.  _

 

_ We didn’t say much of anything as she pushed me out the door. I got in my baby on autopilot, blindly following the direction she gave. Not even feeling the smooth leather handle under my tight grip. I only seemed to snap back into myself when she had me turn in to a familiar lot. _

 

_ Charlie thought my gobsmacked look was funny. Laughing all the way around the back of the diner. _

 

_ “Really?” Was all I managed to say as she knocked a tune on the back entrance.  _

 

_ The door swung open to reveal a rough looking man, apron tied loosely around his large frame. He looked me up and down with a raised brow. _

 

_ “Castiel’s man? Never thought I’d see you on this side of the shop, brother.”  _

 

_ “I’m not Castiel’s—” _

 

_ The eyebrow raised a smidge higher, Benny’s blue eyes twinkling.  _

 

_ I huffed, faintly recalling the intense staring contest I had with Cas over pie the other day. “Charlie said you’re the guy to go to for a good gat.” _

 

_ Benny grabbed my arm. My instincts kicked in, twisting out of his grip. Pocket knife out and pointed at his throat before he could react.  _

 

_ “Whoa there, hey, I just don’t want you gabbing about my side business on the street.” The ‘diner owner’ said, raising his hands. _

 

_ I slid my knife back into the inside of my jacket, trying not to show my embarrassment. Charlie was looking wide-eyed between us. _

 

_ “I suppose you should let us in then, Big Ben.” She said. _

 

_ As I walked inside, it seemed like a perfectly average kitchen. Nothing like the ‘arms stash bigger than Azazel’s ego’ Charlie had gone on about. Benny ushered them in to a back storage room, pulling back a faded carpet to reveal a hatch in the floor. Clever, but I’d more likely expect booze than guns. _

 

_ “So, what did you come to buy?” _

 

_ “Actually,” Charlie cut in before Dean could open his mouth, “We came with a business proposition. One of...mutual assurance.” _

 

_ There was a long pause as Benny looked between them. I could almost hear a clock ticking down the seconds. There was no time to mince words. _

 

_ “Charlie said you wanted to skip town.” I said. Benny, for all his brawn, looked a little sheepish. _

 

_ “Not me, my wife’s the one who—well she doesn’t exactly approve of my side of the business. She doesn’t want anyone comin’ after us, though.” _

 

_ “Naturally.” Charlie said brashly, dress swishing around her legs as she looked into the open hatch. Her red lips gave out a low whistle. _

 

_ “We can give you a reason to leave. If you give us some power and a place to host a pow-wow.” I said. _

 

_ Benny gave me another once over. Inspecting, just like Cas did. Whatever he saw he must have liked because he readily showed us down to the basement. Listening to Charlie’s plan while handing us cake boxes full of bullets and Tommy guns. All of it was loaded into the back of my car.  _

 

_ “Next stop! Dreamy blue eyes!” Charlie said once they loaded up. I rolled my eyes as we headed toward Cas’ place. Ignoring the tightly wound anticipation that wasn’t solely the fault of the upcoming fight. _

 

Only Cas hadn’t been home. And the Trouble Boys hadn’t been as clean as they thought. Not when I knew their patterns. So we’d scrapped the plan, and gone in with shiny new guns. Come hell or high water.

 

Somehow Cas, bless him, used a silver tongue to get us in a less compromising position. I could only pray that our plan worked without him in the know. Charlie had convinced me that the resentment between Azazel and Lucian was personal enough for them to both come out of the woodworks. I damned well hoped so if we even had a chance of sorting them out.

 

I was ready as I’d ever be for this mess to end. 

 

Only one thing I hadn’t accounted for: I should have listened to Charlie. I should have seen it coming. Would have too, if I’d have looked at him in that meeting. If he was showing the same thing in his baby blues as he did later.

 

How willing Cas was to save me.


End file.
